20 Alumni Stories - Caleb Kapusinski

20 Alumni Stories - Caleb Kapusinski

From An Examined Education by The Cambridge School

May 22, 2026 · 10 min · Season 7 · Episode 20

About this episode

Caleb Kapusinski shares his experiences and insights from his time at Cambridge and how they shaped his approach to work and life.

Caleb Kapusinski graduated with the class of 2021 and now works in sales as an account manager for a general contractor. His episode is organized around two convictions he has carried into the workforce and has not stopped thinking about since. The first is that a smaller school creates space for a fuller person. At Cambridge, Caleb played basketball, ran cross country, performed in theater, and served in house leadership, not because he was exceptional in all of those fields, but because the school was small enough to say yes to all of it. He believes that habit of saying yes is increasingly rare, and increasingly valuable. The second is that Cambridge taught him to ask why. In his work, that translates to getting past a client's first answer to find the real problem underneath. In the classroom, it meant Socratic discussions oriented not toward the right answer but toward genuine understanding. The two convictions are, he argues, more related than they appear: a well-rounded person who knows how to ask good questions is, in his experience, exactly what the labor market is not producing and very much needs.

People in this episode

Guest: Caleb Kapusinski

Topics covered

  • alumni stories
  • education
  • personal development
  • workforce skills
  • Socratic method

Keywords

  • Caleb Kapusinski
  • Cambridge School
  • education
  • sales
  • Socratic discussions
  • personal growth
  • workforce

Mentioned in this episode

Organizations: Cambridge

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